Title: Five Cays Adventure Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/11672/d2d90a11-08a9-4e50-887d-b91554f7945e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Five Cays Adventure Vacations ## Book a Adventure Hotel + Flight or Car together to unlock savings ## Top Adventure vacation packages in Five Cays Price found within the past 48 hours. Click for updated prices. ![Dream Villas Provo](https://images.trvl-media.com/lodging/97000000/96370000/96368700/96368651/a01ea79e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dream Villas Provo Save 100% on your flight $1,973 per person Jun 2 - Jun 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9/10 Wonderful! (58 reviews) Excellent location. Walking distance to 2 restaurants, small store across street. Very clean and modern. Comfortable beds. Everything you need for a relaxing beach vacation! Reviewed on Feb 26, 2026 ![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beachfront at Windsong on the Reef Grace Bay Save 100% on your flight $2,762 per person May 25 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9.2/10 Wonderful! (122 reviews) I was worried about our stay having read previous travelers reviews - but my whole family loved our stay at windsong. The property was in great shape, clean and tidy. Lots of towels on the loungers well before we were up. Plenty of room for everyone to get a great seat on the beach or by the pools. The staff were very friendly and kind - shout out to Travis! The food was fine, breakfast was great and worth the money and we did several lunches and one dinner. Expect all food to be expensive no matter where you eat, you’re on a tiny island that needs to import everything. We will definitely stay here again! Reviewed on Mar 17, 2026 ![Windsong on the Reef](https://images.trvl-media.com/lodging/3000000/2430000/2422200/2422198/76aaffd4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Windsong on the Reef Grace Bay Save 100% on your flight $1,996 per person May 25 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9.2/10 Wonderful! (1,026 reviews) The property is beautiful and very well maintained. The rooms are excellent, though we did have an issue with our oven—it wasn’t working. The staff responded quickly and tried to fix it, but we were without an oven for two of our three days, which meant we had to buy food instead of cooking our planned meals. They did make up for the inconvenience with a $50 credit and a complimentary bottle of wine. The beach itself isn’t very wide, but being right on the reef makes for fantastic snorkeling. The beach chairs and umbrellas are great, and the staff takes care of setting everything up for you. The continental breakfast was a perfect way to start each day, especially with the option to choose items from the menu up to an $18 credit. We used the shuttle to get to the grocery store, though bikes are also available. Happy hour featured excellent drinks. The location is somewhat remote—far from other resorts and shopping—so you’ll need to rent a car or take a taxi if you plan to explore. That said, the seclusion made for a peaceful and very quiet stay, which we really enjoyed. I would definitely stay here again. Reviewed on Mar 18, 2026 ![The Park at Grace Bay](https://images.trvl-media.com/lodging/121000000/120070000/120063400/120063392/08207d46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Park at Grace Bay Grace Bay Save 100% on your flight $2,901 per person May 25 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) No reviews ![The Shore Club Turks and Caicos](https://images.trvl-media.com/lodging/16000000/15440000/15438900/15438835/fb1fd0ea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shore Club Turks and Caicos Long Bay Save 100% on your flight $3,159 per person May 25 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9.4/10 Exceptional! (907 reviews) Awesome resort! Restaurants were great too. Rooms were clean with nice views. Pools and amenities were exceptional. The beach was wonderful, lots of activities if you choose. Entire staff was helpful, Khem, Sley, Love, Fortune, David... too many to mention, all great. Excellent location for relaxation and peace and quiet. Atmosphere was relaxing and comfortable. Good value. Reviewed on Mar 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Five Cays [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure vacations in Five Cays Price found within the past 48 hours. Click for updated prices. ![Rock House](https://images.trvl-media.com/lodging/73000000/72070000/72061500/72061427/779a17b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Rock House Save 100% on your flight $2,709 per person May 25 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9.6/10 Exceptional! (379 reviews) Enjoyed the stay - pool, beach and staff were excellent - will come back again for sure! Reviewed on Mar 18, 2026 ![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beachfront at Windsong on the Reef Grace Bay Save 100% on your flight $2,762 per person May 25 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9.2/10 Wonderful! (122 reviews) I was worried about our stay having read previous travelers reviews - but my whole family loved our stay at windsong. The property was in great shape, clean and tidy. Lots of towels on the loungers well before we were up. Plenty of room for everyone to get a great seat on the beach or by the pools. The staff were very friendly and kind - shout out to Travis! The food was fine, breakfast was great and worth the money and we did several lunches and one dinner. Expect all food to be expensive no matter where you eat, you’re on a tiny island that needs to import everything. We will definitely stay here again! Reviewed on Mar 17, 2026 ![The Shore Club Turks and Caicos](https://images.trvl-media.com/lodging/16000000/15440000/15438900/15438835/fb1fd0ea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shore Club Turks and Caicos Long Bay Save 100% on your flight $3,159 per person May 25 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9.4/10 Exceptional! (907 reviews) Awesome resort! Restaurants were great too. Rooms were clean with nice views. Pools and amenities were exceptional. The beach was wonderful, lots of activities if you choose. Entire staff was helpful, Khem, Sley, Love, Fortune, David... too many to mention, all great. Excellent location for relaxation and peace and quiet. Atmosphere was relaxing and comfortable. Good value. Reviewed on Mar 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Five Cays [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure vacations in Five Cays Price found within the past 48 hours. Click for updated prices. ![Dream Villas Provo](https://images.trvl-media.com/lodging/97000000/96370000/96368700/96368651/a01ea79e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dream Villas Provo Save 100% on your flight $1,603 per person May 11 - May 14 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9/10 Wonderful! (58 reviews) Excellent location. Walking distance to 2 restaurants, small store across street. Very clean and modern. Comfortable beds. Everything you need for a relaxing beach vacation! Reviewed on Feb 26, 2026 ![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beachfront at Windsong on the Reef Grace Bay Save 100% on your flight $1,610 per person May 11 - May 14 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9.2/10 Wonderful! (122 reviews) I was worried about our stay having read previous travelers reviews - but my whole family loved our stay at windsong. The property was in great shape, clean and tidy. Lots of towels on the loungers well before we were up. Plenty of room for everyone to get a great seat on the beach or by the pools. The staff were very friendly and kind - shout out to Travis! The food was fine, breakfast was great and worth the money and we did several lunches and one dinner. Expect all food to be expensive no matter where you eat, you’re on a tiny island that needs to import everything. We will definitely stay here again! Reviewed on Mar 17, 2026 ![The Park at Grace Bay](https://images.trvl-media.com/lodging/121000000/120070000/120063400/120063392/08207d46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Park at Grace Bay Grace Bay Save 100% on your flight $1,619 per person May 11 - May 14 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) No reviews Don't see what you're looking for? See all available trips from Columbus to Five Cays [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure vacations in Five Cays Price found within the past 48 hours. Click for updated prices. ![Dream Villas Provo](https://images.trvl-media.com/lodging/97000000/96370000/96368700/96368651/a01ea79e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dream Villas Provo Save 100% on your flight $1,897 per person Jun 8 - Jun 12 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9/10 Wonderful! (58 reviews) Excellent location. Walking distance to 2 restaurants, small store across street. Very clean and modern. Comfortable beds. Everything you need for a relaxing beach vacation! Reviewed on Feb 26, 2026 ![The Park at Grace Bay](https://images.trvl-media.com/lodging/121000000/120070000/120063400/120063392/08207d46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Park at Grace Bay Grace Bay $2,103 per person Apr 21 - Apr 25 found 1 day ago Roundtrip flight included Boston (BOS) to Providenciales (PLS) No reviews ![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beachfront at Windsong on the Reef Grace Bay Save 100% on your flight $2,044 per person Jun 8 - Jun 12 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Providenciales (PLS) 9.2/10 Wonderful! (122 reviews) I was worried about our stay having read previous travelers reviews - but my whole family loved our stay at windsong. The property was in great shape, clean and tidy. Lots of towels on the loungers well before we were up. Plenty of room for everyone to get a great seat on the beach or by the pools. The staff were very friendly and kind - shout out to Travis! The food was fine, breakfast was great and worth the money and we did several lunches and one dinner. Expect all food to be expensive no matter where you eat, you’re on a tiny island that needs to import everything. We will definitely stay here again! Reviewed on Mar 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Five Cays [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find awesome Five Cays adventure vacations #### How can I book the best Five Cays adventure trips? Choose your own adventure in Five Cays, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun. #### How can I plan the perfect Five Cays family adventure vacation? Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Five Cays. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning. #### Can I book all-inclusive Five Cays adventure vacation packages? By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway. #### Why should I book a Five Cays adventure vacation for couples? Book a Five Cays couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond. #### How can I find the best deals on adventure packages in Five Cays? It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals. #### Can I book an adventure vacation package in Five Cays with free cancellation and/or flexible dates? Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility. #### Why should I book a Five Cays adventure trip with Expedia? Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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](https://expedia.com/Cheap-Flights-To-Five-Cays.d11672.Travel-Guide-Flights)[ Five Cays Hotels ](https://expedia.com/Five-Cays-Hotels.d11672.Travel-Guide-Hotels)[ Vacation Rentals in Five Cays ](https://expedia.com/Five-Cays-Vacation-Rentals.d11672.Travel-Guide-VacationRentals)[ Car Rentals in Five Cays ](https://expedia.com/Car-Rentals-In-Five-Cays.d11672.Car-Rental-Guide)[ Five Cays Vacations ](https://expedia.com/Five-Cays.d11672.Destination-Travel-Guides)[ Things to do in Five Cays ](https://expedia.com/Things-To-Do-In-Five-Cays.d11672.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.